Diethyl chlorophosphate → HCID 131722626, compound

Participants

Reaction Steps

The title compound was prepared by reaction of BocTyrOBzl (371 mg, 1 mmol) and diethylphosphorochloridate (258 mg, 1.5 mmol) with an excess of NaH (60% in mineral oil) in dry dioxane for 3.5 h at 50° C. under argon atmosphere The solvent was concentrated in vacuo and the residue was dissolved in EtOAc and washed several times with a 5% solution of NaHCO3, a 10% solution of citric acid and a solution of satured NaCl. The organic phase was dried (Na2SO4) and concentrated, giving an oil 254 mg (50% yield), that was used without purification for the next step. FAB mass spectroscopy: m/z 508 [MH]+, 530 [MNa]+. H1NMR (200 Mhz, CDCl3) d (ppm)=7.4-6.85 (m, 9H, aromatics), 5.1 (d, 2H, COOCH2—F), 4.6 (m, 1H, N—CH—CO), 4.3-4 (m, 4H, P—O—CH2—CH3), 3 (t, 2H, CH—CH2—F), 1.4 (m, 15H, CH3− CH2+ tBu).

Provenance & Evidence